Download Pyruvic acid

Pyruvic acid
1
Pyruvic acid
Pyruvic acid
Identifiers
CAS number
127-17-3
ChemSpider
1031
[1]
[2]
SMILES
Properties
Molecular formula
C3H4O3
Molar mass
88.06 g/mol
Density
1.250 g/cm³
Melting point
11.8 °C, 285 K, 53 °F
Boiling point
165 °C, 438 K, 329 °F
Acidity (pKa)
2.49 at 25 °C
Related compounds
Other anions
pyruvate ion
Related keto-acids, carboxylic acids
acetic acid
glyoxylic acid
oxalic acid
propionic acid
acetoacetic acid
Related compounds
propionaldehyde
glyceraldehyde
methylglyoxal
sodium pyruvate
(what is this?) (verify)
[3]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
Pyruvic acid
2
Pyruvic acid (CH3COCOOH) is an organic acid. It is also a ketone, as well as being the simplest alpha-keto acid.
The carboxylate (COOH) ion (anion) of pyruvic acid, CH3COCOO-, is known as pyruvate, and is a key intersection
in several metabolic pathways. It can be made from glucose through glycolysis, supplies energy to living cells in the
citric acid cycle (also known as the Krebs cycle), and can also be converted to carbohydrates via gluconeogenesis, to
fatty acids or energy through acetyl-CoA, to the amino acid alanine and to ethanol.
Chemistry
Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid. It is miscible with water, and soluble in
ethanol and diethyl ether. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and
potassium hydrogen sulfate, by the oxidation of propylene glycol by a strong oxidizer (eg. potassium permanganate
or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:
CH3COCl + KCN → CH3COCN
CH3COCN → CH3COCOOH
Biochemistry
Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose
known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvate, which are then used to
provide further energy, in one of two ways. Pyruvate is converted into acetyl-coenzyme A, which is the main input
for a series of reactions known as the Krebs cycle. Pyruvate is also converted to oxaloacetate by an anaplerotic
reaction which replenishes Krebs cycle intermediates; alternatively, the oxaloacetate is used for gluconeogenesis.
These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology,
jointly with Fritz Lipmann, for research into metabolic processes. The cycle is also called the citric acid cycle,
because citric acid is one of the intermediate compounds formed during the reactions.
If insufficient oxygen is available, the acid is broken down anaerobically, creating lactate in animals and ethanol in
plants and microorganisms. Pyruvate from glycolysis is converted by anaerobic respiration to lactate using the
enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation, or to acetaldehyde and then to
ethanol in alcoholic fermentation.
Pyruvate is a key intersection in the network of metabolic pathways. Pyruvate can be converted into carbohydrates
via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine and to ethanol. Therefore
it unites several key metabolic processes.
The
pyruvic
acid
derivative
bromopyruvic acid is being studied for
potential cancer treatment applications
by researchers at Johns Hopkins
University in ways that would support
the Warburg hypothesis on the cause(s)
of cancer.
Reference ranges for blood tests, comparing blood content of pyruvate (shown in violet
near middle) with other constituents.
Pyruvate production by glycolysis
In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly
exergonic and irreversible; in gluconeogenesis it takes two enzymes, pyruvate carboxylase and PEP carboxykinase,
to catalyze the reverse transformation of pyruvate to PEP.
Pyruvic acid
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phosphoenolpyruvate pyruvate kinase
ADP
ATP
ADP
ATP
pyruvate
pyruvate kinase
Compound C00074 [4] at KEGG Pathway Database. Enzyme 2.7.1.40
C00022 [6] at KEGG Pathway Database.
[5]
at KEGG Pathway Database. Compound
Pyruvate decarboxylation to acetyl CoA
Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.
pyruvate
pyruvate dehydrogenase complex
acetyl-CoA
CoA + NAD+ CO2 + NADH + H+
Pyruvate carboxylation to oxaloacetate
Carboxylation by the pyruvate carboxylase produces oxaloacetate.
pyruvate
pyruvate carboxylase
oxaloacetate
ATP + CO2 ADP + Pi
Transamination by the alanine aminotransferase
pyruvate
alanine transaminase
glutamate α-ketoglutarate
glutamate α-ketoglutarate
alanine
Pyruvic acid
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Reduction to lactate
Reduction by the lactate dehydrogenase produces lactate.
pyruvate
lactate dehydrogenase
NADH
NAD+
NADH
NAD+
lactate
Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [7]
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Citric acid cycle edit [8]
Origin of life
Current evolutionary theory on the origin of life posits that the first organisms were anaerobic because the
atmosphere of prebiotic Earth was, in theory, almost barren of diatomic oxygen. As such, requisite biochemical
materials must have preceded life. In vitro, iron sulfide at sufficient pressure and temperature catalyzes the formation
of pyruvate. Thus, argues Günter Wächtershäuser, the mixing of iron-rich crust with hydrothermal vent fluid is
suspected of providing the fertile basis for the formation of life.
Pyruvic acid
See also
• Pyruvate scale
Notes
[1]
[2]
[3]
[4]
[5]
[6]
[7]
http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=127-17-3
http:/ / www. chemspider. com/ 1031
http:/ / en. wikipedia. org/ wiki/ %3Apyruvic_acid
http:/ / www. genome. jp/ dbget-bin/ www_bget?compound+ C00074
http:/ / www. genome. jp/ dbget-bin/ www_bget?enzyme+ 2. 7. 1. 40
http:/ / www. genome. jp/ dbget-bin/ www_bget?compound+ C00022
The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78" (http:/ / www. wikipathways. org/ index. php/
Pathway:WP78). .
[8] http:/ / www. wikipathways. org/ index. php/ Pathway:WP78
References
• Cody, G. D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder, H. S.; Jr, (2000).
"Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate". Science 289 (5483): 1337.
doi:10.1126/science.289.5483.1337. PMID 10958777.
7
Article Sources and Contributors
Article Sources and Contributors
Pyruvic acid Source: http://en.wikipedia.org/w/index.php?oldid=394294993 Contributors: AlexanderPico, Antandrus, Antonio Lopez, Arbitrarily0, Arcadian, Arkwatem, Beetstra,
Benjah-bmm27, BorisTM, Breez, Bunnyhop11, Cacycle, Carmichael95, Casforty, Chem-awb, Chino, Cldick, CopperKettle, Crystallina, D.O.C.rEzKaWy, Dakatone, Dantelebeau, Dono,
Drphilharmonic, Dwmyers, Edgar181, Eloy, Emijrp, Engreida, Flobach, Freestyle-69, GraybeardBiochemist, Gryphn, Hannes Röst, Henrik, IW.HG, Isnow, Javascholar, Johner, Jrockley,
Keilana, Ketsuekigata, Kingpin13, Kostisl, Kupirijo, Levil, Logan, Makeemlighter, Marcelo1229, MarnetteD, Master gopher, Michael Shields, Michall, Mihai, Mikael Häggström, Mike65535,
Minesweeper.007, Nairobiny, Nbauman, Nick Number, Nomad2u001, Oatmeal batman, Ojigiri, PGWG, PhilKnight, Polylepis, Pro crast in a tor, RandomP, Rhetth, Rifleman 82, Robbie098,
Roo1812, ScAvenger lv, SchuminWeb, Securiger, Slashme, Solon.KR, Spoladore, Strawbaby, ThinkerThoughts, Timothykinney, Una Smith, Wickey-nl, Wwallacee, Yikrazuul, Yurylv,
Zephyris, 93 anonymous edits
Image Sources, Licenses and Contributors
File:Pyruvic-acid-2D-skeletal.png Source: http://en.wikipedia.org/w/index.php?title=File:Pyruvic-acid-2D-skeletal.png License: Public Domain Contributors: Benjah-bmm27, Kpengboy
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image:phosphoenolpyruvate_wpmp.png Source: http://en.wikipedia.org/w/index.php?title=File:Phosphoenolpyruvate_wpmp.png License: Public Domain Contributors: Richard Wheeler
(Zephyris)
image:pyruvate_wpmp.png Source: http://en.wikipedia.org/w/index.php?title=File:Pyruvate_wpmp.png License: Public Domain Contributors: Richard Wheeler (Zephyris)
image:Biochem_reaction_arrow_reversible_YYYY_horiz_med.png Source: http://en.wikipedia.org/w/index.php?title=File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.png
License: GNU Free Documentation License Contributors: Richard Wheeler (Zephyris)
image:acetyl_co-A_wpmp.png Source: http://en.wikipedia.org/w/index.php?title=File:Acetyl_co-A_wpmp.png License: Public Domain Contributors: Richard Wheeler (Zephyris)
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image:Oxaloacetate_wpmp.png Source: http://en.wikipedia.org/w/index.php?title=File:Oxaloacetate_wpmp.png License: Public Domain Contributors: Richard Wheeler (Zephyris)
image:alanine_wpmp.png Source: http://en.wikipedia.org/w/index.php?title=File:Alanine_wpmp.png License: GNU Free Documentation License Contributors: Original uploader was
Zephyris at en.wikipedia
image:Lactic-acid-skeletal.svg Source: http://en.wikipedia.org/w/index.php?title=File:Lactic-acid-skeletal.svg License: Public Domain Contributors: User:NEUROtiker
Image:TCACycle_WP78.png Source: http://en.wikipedia.org/w/index.php?title=File:TCACycle_WP78.png License: Creative Commons Attribution 3.0 Contributors: Alexander Pico, Thomas
Kelder, Martijn van Iersel, Kristina Hanspers, Kdahlquist, Nick Fidelman
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